EP0243205A1 - Plaque électrophotographique - Google Patents

Plaque électrophotographique Download PDF

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Publication number
EP0243205A1
EP0243205A1 EP87303655A EP87303655A EP0243205A1 EP 0243205 A1 EP0243205 A1 EP 0243205A1 EP 87303655 A EP87303655 A EP 87303655A EP 87303655 A EP87303655 A EP 87303655A EP 0243205 A1 EP0243205 A1 EP 0243205A1
Authority
EP
European Patent Office
Prior art keywords
naphthalocyanine
compound
bis
formula
silicon
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP87303655A
Other languages
German (de)
English (en)
Other versions
EP0243205B1 (fr
Inventor
Sigeru Hayashida
Seiji Kamisuwa Apartment 402 Tai
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Resonac Corp
Original Assignee
Hitachi Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP15012686A external-priority patent/JPS635093A/ja
Application filed by Hitachi Chemical Co Ltd filed Critical Hitachi Chemical Co Ltd
Publication of EP0243205A1 publication Critical patent/EP0243205A1/fr
Application granted granted Critical
Publication of EP0243205B1 publication Critical patent/EP0243205B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/045—Special non-pigmentary uses, e.g. catalyst, photosensitisers of phthalocyanine dyes or pigments
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/04—Esters of silicic acids
    • C07F7/06—Esters of silicic acids with hydroxyaryl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/073—Preparation from isoindolenines, e.g. pyrrolenines
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0696—Phthalocyanines

Definitions

  • Fig. l is absorption spectra of a naphthalo­cyanine having two trihexylsiloxy groups bonded to the central metal silicon synthesized in Synthesis Example l (solid line), and a phthalocyanine similar to it (dotted line).
  • Fig. 2 is an absorption spectrum of a vapor depos­ited film of naphthalocyanine having two trihexylsiloxy groups bonded to the central metal silicon synthesized in Synthesis Example l.
  • the naphthalocyanine compound of the formula (I) can be produced by reacting dihydroxy-silicon naphthalocyanine of the formula: with a compound of the formula: R1R2R3SiX (III) wherein R1, R2 and R3 are as defined above; and X is a hydroxyl group or a halogen with heating.
  • Dihydroxysilicon naphthalocyanine is a known compound and can be produced, for example, by the method described in J. Am. Chem. Soc. vol. l06, pp7404- (l984) and the route (A) as shown below:
  • the dihydroxysilicon naphthalocyanine of the formula (II) is reacted with a compound of the formula (III), for example, a chlorosilane compound of the formula: R1R2R3SiCl (III ⁇ ) wherein R1, R2 and R3 are as defined above, at l40 to l50°C for l.0 to 3.0 hours, e.g. l.5 hours to yield the naphthalocyanine compound of the formula (I) wherein the two siloxy groups of the formula: R1R2R3Si-O- are bonded to the central metal silicon.
  • a compound of the formula (III) for example, a chlorosilane compound of the formula: R1R2R3SiCl (III ⁇ ) wherein R1, R2 and R3 are as defined above, at l40 to l50°C for l.0 to 3.0 hours, e.g. l.5 hours to yield the naphthalocyanine compound of the formula (
  • Examples of the siloxy group of the formula: R1R2R3Si-O- are a dimethylsiloxy group, a trimethylsiloxy group, a dimethyoxymethylsiloxy group, a dimethylpropyl­siloxy group, a t-butyldimethylsiloxy group, a triethyl­siloxy group, a triethoxysiloxy group, a tripropylsiloxy group, a dimethyloctylsiloxy group, a tributylsiloxy group, a trihexylsiloxy group, etc.
  • the photoconductive layer is a layer containing an organic photoconductive substance, and can be in the form of a film of an organic photoconductive substance, a film containing an organic photoconductive substance and a binder, a complex type film comprising a charge generation layer and a charge transport layer, etc.
  • the naphthalocyanine of the formula (I) is used as an essential component. It is possible to co-use one or more conventional photoconductive substances. It is preferable to use the naphthalocyanine of the formula (I) alone or in combination with one or more organic pigments generating charge together with one or more charge transport substances.
  • the naphthalocyanine of the formula (I) and the organic pigments generating charge are contained, and in the charge transport layer, the charge transport substances are contained.
  • organic pigment which is included in the charge generation layer for charge generation
  • organic pigments there can be used azoxybenzenes, disazos, trisazos, benzimida­zoles, multi-ring quinones, indigoids, quinacridones, metallic or non-metallic phthalocyanines having various crystal structures, perylenes, methines, etc., these pigments being known for charge generation.
  • These pigments can be used alone or as a mixture thereof.
  • These pigments are, for example, disclosed in British Patent Nos. l,370,l97, l,337,222, l,337,224 and l,402,967, U.S. Patent Nos.
  • the naphthalocyanine compound of the formula (I) with or without an organic pigment which can generates charge is contained in the charge generation layer which may contain the binder in an amount of 500% by weight or less based on the weight of the organic pigment, or contain the additives in an amount of 5% by weight or less based on the weight of the naphthalocyanine compound of the formula (I) or a total amount of the naphthalocyanine compound of the formula (I) and the organic pigment.
  • the charge trans­port substance is contained in the charge transport layer which may contain the binder in an amount of 500% by weight or less based on the weight of the charge transport substance.
  • the resins there is no particular limitation to the resins, so long as they can form insulating films under normal conditions or can form films by curing with heat and/or light.
  • the electroconductive support for forming an electroconductive layer there can be used paper or plastic films subjected to the electroconductivity treatment, plastic films clad with a metal foil such as aluminum, metal plates, and the like.
  • Bis(dimethylpropylsiloxy)silicon naphthalo­cyanine was synthesized in the same manner as described in Synthesis Example l except for using dimethyl­propylsilyl chloride in place of trihexylsilyl chloride in the step (5).
  • Bis(tripropylsiloxy)silicon naphthalocyanine was synthesized in the same manner as described in Synthesis Example l except for using tripropylsilyl chloride in place of trihexylsilyl chloride in the step (5).
  • the half decay exposure amount (the product of a time required for making the potential retention rate l/2 by the light intensity) was 20 mJ/m2.
  • An electrophotographic plate was produced in the same manner as described in Comparative Example l except for using p-diethylaminobenzaldehyde-disphenyl­hydrazone as a charge transport substance in place of l-phenyl-3-(p-diethylaminostyryl)-5-(p-diethylamino­phenyl)pyrazoline.
  • the half decay exposure amount of the electrophotographic plate using the monochromatic light of 800 nm in the near infrared region measured in the same manner as described in Example l was 3200 mJ/m2.
  • Each solution was prepared by dissolving a phthalocyanine wherein two trihexylsiloxy groups were bonded to the central metal silicon or a naphthalocyanine compound wherein two trihexylsiloxy groups were bonded to the central metal silicon (the naphthalocyanine compound synthesized in Synthesis Example l) in chloroform to measure an absorption spectrum.
  • the results are shown in Fig. l.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photoreceptors In Electrophotography (AREA)
EP87303655A 1986-04-24 1987-04-24 Plaque électrophotographique Expired - Lifetime EP0243205B1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP9533786 1986-04-24
JP95337/86 1986-04-24
JP15012686A JPS635093A (ja) 1986-06-26 1986-06-26 ビス（トリアルキルシロキシ）シリコンナフタロシアニン及びその製造法
JP150126/86 1986-06-26

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP89122030.3 Division-Into 1989-11-29

Publications (2)

Publication Number Publication Date
EP0243205A1 true EP0243205A1 (fr) 1987-10-28
EP0243205B1 EP0243205B1 (fr) 1991-01-30

Family

ID=26436592

Family Applications (2)

Application Number Title Priority Date Filing Date
EP89122030A Expired - Lifetime EP0375967B1 (fr) 1986-04-24 1987-04-24 Composés de naphtalo-cyanines et procédé pour leur préparation
EP87303655A Expired - Lifetime EP0243205B1 (fr) 1986-04-24 1987-04-24 Plaque électrophotographique

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP89122030A Expired - Lifetime EP0375967B1 (fr) 1986-04-24 1987-04-24 Composés de naphtalo-cyanines et procédé pour leur préparation

Country Status (3)

Country Link
US (3) US4749637A (fr)
EP (2) EP0375967B1 (fr)
DE (2) DE3789243T2 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0357360A2 (fr) * 1988-08-31 1990-03-07 Hitachi Chemical Co., Ltd. Dérivés de naphtalocyanine, leur préparation, et milieu d'enregistrement optique les utilisant
US4927735A (en) * 1987-01-07 1990-05-22 Hitachi Chemical Company, Ltd. Novel naphthalocyanine dye, method for preparing the same, and optical information recording medium employing the same
US5484685A (en) * 1988-10-25 1996-01-16 Hitachi, Ltd. Naphthalocyanine derivatives, production thereof, optical recording medium using the same, and production thereof

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4749637A (en) * 1986-04-24 1988-06-07 Hitachi Chemical Co., Ltd. Electrophotographic plate with silicon naphthalocyanine
US4863821A (en) * 1986-07-07 1989-09-05 Minolta Camera Kabushiki Kaisha Photosensitive member comprising charge generating layer and charge transporting layer having amorphous carbon
JPS63186251A (ja) * 1987-01-29 1988-08-01 Hitachi Chem Co Ltd 金属ナフタロシアニン誘導体膜及び電子写真感光体
US5000831A (en) * 1987-03-09 1991-03-19 Minolta Camera Kabushiki Kaisha Method of production of amorphous hydrogenated carbon layer
EP0288876B1 (fr) * 1987-04-22 1994-07-20 Hitachi Chemical Co., Ltd. Plaque électrophotographique
DE3810956A1 (de) * 1988-03-31 1989-10-12 Basf Ag Neue siliciumnaphthalocyanine sowie duenne strahlungsempfindliche beschichtungsfilme, die diese verbindungen enthalten
US5087390A (en) * 1989-04-04 1992-02-11 Hoechst Celanese Corp. Tetraazaporphyrin dye mixtures
US5606045A (en) * 1990-05-15 1997-02-25 Diatron Corporation Nucleic acid probes and methods
JPH0776837B2 (ja) * 1990-10-26 1995-08-16 富士ゼロックス株式会社 電子写真感光体
JPH07507074A (ja) * 1991-11-08 1995-08-03 イーストマン ケミカル カンパニー 近赤外発螢光団を有する熱可塑性材料の標識方法
US7083984B2 (en) 1993-09-24 2006-08-01 Biosite, Inc. Hybrid phthalocyanine derivatives and their uses
US5824799A (en) * 1993-09-24 1998-10-20 Biosite Diagnostics Incorporated Hybrid phthalocyanine derivatives and their uses
US7322927B2 (en) 1993-09-24 2008-01-29 Biosite, Inc. Hybrid phthalocyanine derivatives and their uses
TWI329662B (en) * 2002-05-17 2010-09-01 Sipix Imaging Inc Novel fluorinated silicon (iv) phthalocyanines and naphthalocyanines for electrophoretic, magnetophoretic or electromagnetophoretic display
JP5216279B2 (ja) 2007-08-23 2013-06-19 富士フイルム株式会社 有機半導体材料、該材料を含む膜、有機電子デバイス及び赤外色素組成物
JP5499990B2 (ja) 2010-08-19 2014-05-21 コニカミノルタ株式会社 静電荷像現像用シアントナー
JP2020518107A (ja) 2017-04-26 2020-06-18 オーティーアイ ルミオニクス インコーポレーテッドＯｔｉ Ｌｕｍｉｏｎｉｃｓ Ｉｎｃ． 表面上のコーティングをパターン化する方法およびパターン化されたコーティングを含むデバイス
US12069938B2 (en) 2019-05-08 2024-08-20 Oti Lumionics Inc. Materials for forming a nucleation-inhibiting coating and devices incorporating same
US12113279B2 (en) 2020-09-22 2024-10-08 Oti Lumionics Inc. Device incorporating an IR signal transmissive region
WO2022123431A1 (fr) 2020-12-07 2022-06-16 Oti Lumionics Inc. Formation de motifs sur une couche conductrice déposée à l'aide de revêtement inhibiteur de nucléation et revêtement métallique sous-jacent

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0050464A2 (fr) * 1980-10-16 1982-04-28 Fujitsu Limited Matériau photosensible pour électrophotographie
EP0129413A1 (fr) * 1983-06-15 1984-12-27 Mita Industrial Co. Ltd. Matériau stratifié photosensible et procédé de sa production

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3816118A (en) * 1964-06-15 1974-06-11 Xerox Corp Electrophotographic element containing phthalocyanine
US3926629A (en) * 1970-03-11 1975-12-16 Xerox Corp Electrophotographic method and plate employing a phthaldcyanine polymer
US4214907A (en) * 1978-01-05 1980-07-29 Mita Industrial Company, Ltd. Photosensitive material for electrophotography having a polyvinyl carbazole derivative, phthalocyanine, and an electron-acceptor
US4131609A (en) * 1978-02-23 1978-12-26 The United States Of America As Represented By The Secretary Of The Navy Silicon-phthalocyanine-siloxy monomers
JPS57148745A (en) * 1981-03-11 1982-09-14 Nippon Telegr & Teleph Corp <Ntt> Lamination type electrophotographic receptor
US4557989A (en) * 1984-09-13 1985-12-10 Xerox Corporation Photoresponsive imaging members with dihydroxy metal phthalocyanine compositions
US4725525A (en) * 1985-02-04 1988-02-16 Hoebbst Celanese Corporation Recording information media comprising chromophores
US4749637A (en) * 1986-04-24 1988-06-07 Hitachi Chemical Co., Ltd. Electrophotographic plate with silicon naphthalocyanine

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0050464A2 (fr) * 1980-10-16 1982-04-28 Fujitsu Limited Matériau photosensible pour électrophotographie
EP0129413A1 (fr) * 1983-06-15 1984-12-27 Mita Industrial Co. Ltd. Matériau stratifié photosensible et procédé de sa production

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 106, November 1984, American Chemical Society B.L.WHEELER et al. "A Silicon Phatalocyanine and a Silicon Naphtalocyanine: Synthesis, Electrochemistry, and Electrogenerated Chemiluminiscence" pages 7404-7410, * Page 7405 ; fig. 1 ; column 2, paragraphs 4-6 * *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4927735A (en) * 1987-01-07 1990-05-22 Hitachi Chemical Company, Ltd. Novel naphthalocyanine dye, method for preparing the same, and optical information recording medium employing the same
EP0357360A2 (fr) * 1988-08-31 1990-03-07 Hitachi Chemical Co., Ltd. Dérivés de naphtalocyanine, leur préparation, et milieu d'enregistrement optique les utilisant
EP0357360A3 (en) * 1988-08-31 1990-07-25 Hitachi Chemical Co., Ltd. Naphthalocyanine derivatives, production thereof and optical recording medium using the same
US5484685A (en) * 1988-10-25 1996-01-16 Hitachi, Ltd. Naphthalocyanine derivatives, production thereof, optical recording medium using the same, and production thereof

Also Published As

Publication number Publication date
EP0375967B1 (fr) 1994-03-02
US5428152A (en) 1995-06-27
US5081236A (en) 1992-01-14
DE3789243D1 (de) 1994-04-07
US4749637A (en) 1988-06-07
EP0375967A1 (fr) 1990-07-04
DE3767752D1 (en) 1991-03-07
DE3789243T2 (de) 1994-06-09
EP0243205B1 (fr) 1991-01-30

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